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(3-(3-Methylureido)phenyl)boronic acid → HCID 86588734, Verbindung

HRID 1063918
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1063918
O1CCCCC1[O:7][NH:8][C:9](=[O:30])[CH2:10][C@@:11]1([C:24]2[S:25][C:26](Br)=[CH:27][CH:28]=2)[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][N:14]([S:20]([CH3:23])(=[O:22])=[O:21])[CH2:13][CH2:12]1.[CH3:31][NH:32][C:33]([NH:35][C:36]1[CH:37]=[C:38](B(O)O)[CH:39]=[CH:40][CH:41]=1)=[O:34]>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:7][NH:8][C:9](=[O:30])[CH2:10][C@@:11]1([C:24]2[S:25][C:26]([C:38]3[CH:39]=[CH:40][CH:41]=[C:36]([NH:35][C:33]([NH:32][CH3:31])=[O:34])[CH:37]=3)=[CH:27][CH:28]=2)[S:17](=[O:18])(=[O:19])[CH2:16][CH2:15][N:14]([S:20]([CH3:23])(=[O:21])=[O:22])[CH2:13][CH2:12]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 2

HCID 22276448(3-(3-Methylureido)phenyl)boronic acidHCID 23402085HCID 23402085, Verbindung

Produkt 1

HCID 86588734HCID 86588734, VerbindungAusbeute 13,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8071
1,2-Dimethoxyethane
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel
HCID 10340Sodium CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of N-(2-tetrahydropyranyloxy)-2-[(S)-7-(5-bromo-2-thienyl)-4-methanesulfonyl-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (230 mg), 3-(methylaminocarbonylamino)phenylboronic acid (123 mg) and tetrakis(triphenylphosphine)palladium(0) (24.4 mg) in a mixture of 1,2-dimethoxyethane (2 ml) and 2M aqueous sodium carbonate solution (0.85 ml) was stirred for 4 hours at 80° C. After cooling to room temperature, the mixture was diluted with ethyl acetate, washed with aqueous saturated sodium bicarbonate and brine, dried over sodium sulfate and concentrated in vacuo. The obtained residue was dissolved in methanol (2 ml) and 10% hydrogen chloride in methanol (0.5 ml) was added thereto. After being stirred for 30 minutes at room temperature, the solution was concentrated in vacuo. The residue was purified with silica gel column chromatography (eluent; 0.5-5% methanol in chloroform) to give N-hydroxy-2-[(S)-7-(5-(3-(methylaminocarbonylamino)-phenyl)-2-thienyl)-4-methanesulfonyl-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (30 mg).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. washwashed with aqueous saturated sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe obtained residue was dissolved in methanol (2 ml)
  6. addition10% hydrogen chloride in methanol (0.5 ml) was added
  7. stirringAfter being stirred for 30 minutes at room temperature
  8. concentrationthe solution was concentrated in vacuo
  9. customThe residue was purified with silica gel column chromatography (eluent; 0.5-5% methanol in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-778b49d90fa146b7bd43de5cfeab5e66
Quelldatensatz
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06967197B2

Notizen zur Reaktion

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